My First Foundation Sprint with an AI Startup: How We Turned Strategic Confusion Into a Testable Hypothesis

“We don’t know what we don’t know until we’re faced with tough questions.”

That’s what I realized halfway through my first Foundation Sprint workshop with the team behind Werd.ai, an AI startup I met through my network. They had come to me with a challenge that sounded familiar: they were on to something big. They had built and launched Werd.ai as an MVP for content strategy, powered by their underlying technology (MAG OS) but were wondering if MAG OS should be a standalone service/product for other use cases entirely.

Instead of traditional consulting calls, I proposed something different: a 2-day Foundation Sprint workshop (created by Jake Knapp & John Zeratsky from Character Capital) to help them explore this strategic question and figure out the best path forward.

“ You know nothing, Jon Snow — Ygritte, Game of Thrones

How We Started

The Werd.ai team showed up ready to work on a Monday morning: the founder, their founding engineer, and marketer. Smart people who’d built a working product powered by sophisticated technology, but needed strategic clarity on how to best leverage what they’d created.

During our pre-workshop call, I’d identified the core issue: they had something powerful in MAG OS and a working product in Werd.ai, but weren’t sure about the best strategic direction moving forward. Should they expand MAG OS into a platform for different use cases, or focus on Werd.ai?

My goal wasn’t to give them a perfect strategy. It was to help them think through their options and find the strategic direction that made the most sense for achieving product-market fit.

Day 2 Pivot

After Day 1, I’d given the team homework. As we explored their strategic options - whether to make MAG OS a standalone platform or expand Werd.ai’s capabilities, it became clear we needed to understand the competitive landscape for both potential directions. So I asked them to go home and research who they’d actually be competing against if they expanded into comprehensive marketing strategy.

The founder came back on Day 2 with new insights: “I did some research last night, and I think we got our competition wrong yesterday.”

I'd anticipated the homework might surface some new insights, but I hadn't expected it to fundamentally shift our entire competitive framework.

Still, this was exactly the kind of deeper thinking the research was meant to unlock. This was exactly why I gave them homework: sometimes teams need to step away to do some deep thinking before they can see clearly.

Instead of pushing forward with our original plan, I made a choice: “Okay, let’s rebuild this. What did you discover?”

That pivot turned out to be the workshop’s turning point.

The Breakthrough: When Everything Clicked

As we rebuilt the competitive landscape, something shifted in the room. The energy went from confusion to clarity.

Here’s what they discovered: although their competitors were different from what they’d initially benchmarked MAG OS against, most of the competition was doing the same thing. All these platforms required users to already have some form of specialized knowledge to use them effectively.

This insight reinforced that MAG OS was going in a totally different direction. Their potential customers wouldn’t need existing expertise since the AI would tell them what to do about their marketing strategy, not just help them execute it.

The team started aligning around this differentiation. Instead of seeing themselves as “another AI tool trying to do strategy,” they began understanding they were building something fundamentally different: a platform that could think strategically for users who didn’t even know what to do or what to start - hopefully paving a clearer path to product-market fit.

This strategic clarity directly informed their product development priorities, helping them understand not just what to build, but why and for whom.

So, instead of making MAG OS a standalone platform for other use cases, they would double down on expanding Werd.ai’s capabilities using MAG OS. They would go from content strategy to comprehensive marketing strategy, serving the same customers but with much more sophisticated multi-agent capabilities.

Key Insights

After two intense days and several walls as well a Miro board filled with sticky notes, here’s what we walked away with:

A Founding Hypothesis they could actually test: Early and growth-stage startups and SMEs that don’t have existing marketing expertise could find value in Werd.ai’s approach. The team will know they’re onto something if 90% of customers they demo the product to decide to pay for it on the spot.

Clear customer segments and where to find them: Instead of “anyone who needs marketing help,” we identified specific company sizes, roles, and even the communities where these people hang out.

A validation framework: Concrete steps to test whether the problem the team solving is important enough for people to pay for.

Team alignment: As the team debriefed, “It was good to have alignment among each other.” They had a shared hypothesis they could prove or disprove.

Time saved: Instead of spending months building something based on assumptions, they had a focused testing plan.

My Reflection

This was my first Foundation Sprint workshop, and I learned as much as the Werd.ai team did:

“We don’t know what we don’t know until we’re faced with the tough questions” is a feature, not a bug. When you have powerful technology like MAG OS, it’s easy to see endless possibilities. But teams often can’t see the strategic trade-offs clearly until challenging questions force them to think through the implications. The moment we started asking the tough questions about market and competitive positioning, the real strategic thinking began.

Time-boxing is crucial (and I need to get better at it). My biggest improvement for next time: enforce those activity time-boxing. Good strategic conversations usually happen when constraints are imposed - sometimes better conversations even.

The best facilitation means knowing when to follow the team’s insight. When the team came back with new competitive research, my instinct was to stick to the plan. But following their research was what led to the strategic breakthrough.

Workshops work because they force decisions. In regular business operations, you can debate strategic direction for months. In a workshop, you have two days to think through your options and make a focused choice about what you want to test. That constraint creates clarity.

What’s Next

This is part 1 of a 2-part series documenting this workshop. Part 2 will be 90 days later (what the team actually tested and what happened).

For founders reading this: What assumptions about your competition, customers, or positioning are you making that you haven’t actually tested? Sometimes the most valuable thing you can do is admit you don’t know... then build a plan to find out.